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Organic Chemistry, 6e (Bruice)

Chapter 13 Mass Spectometry, Infrared Spectroscopy, and UV/Vis Spectroscopy


1) Which of the following molecular changes is necessary for mass spectrometry to occur?
A) excitation of an electron from the ground state to higher energy state
B) change of alignment of an electron in a magnetic field
C) change of alignment of a proton in a magnetic field
D) loss of an electron
E) molecular vibration
2) Which of the following statements is true about a molecular ion?
A) It is a compound that lost a pair of electrons.
B) It is a compound that gained a pair of electrons.
C) It is a compound that gained one electron.
D) It is a compound that lost one electron.
E) It is a compound that carries a free radical and a negative charge.
3) Which of the following statements best describes the meaning of the following species:
[CH3CH2CH3] + ?
A) It is the molecular ion of propane.
B) It is the parent ion of propane.
C) It is the radical cation of propane.
D) The m/z value is 44.
E) all of the above
4) Which of the following m/z values is the molecular ion for 2-butanone?

A) 15
B) 29
C) 43
D) 57
E) 72
5) What does m/z stand for and what does it mean?
Answer: The m stands for the mass and z for the charge. Since most fragments have a charge of
+1, m/z is the molecular weight of the fragment.
Section: 13-1
6) Describe the fate of a molecule from introduction to detection in a mass spectrometer.
Answer: Upon introduction, sample molecules are ionized by an electron beam passing through
a vacuum chamber. The resulting radical cation and fragment cations are accelerated into the
flight tube of the magnet by a negatively charged plate. In the flight tube, the path of the ions is
bent by the existing magnetic field. For a given magnetic field strength, only one m/z will be
bent in such a way that its path matches the curvature of the tube and reaches the detector. The
entire m/z range is scanned by varying the strength of the magnetic field.

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7) Which of the following statements best explains the information we can gain from mass
spectrometry?
A) It allows us to determine the number of protons in a compound.
B) It allows us to determine the kinds of functional groups in a compound.
C) It allows us to determine the molecular weight and the mass of some fragments of a
compound.
D) It allows us to determine the presence and nature of a carbocation in the compound.
E) It allows us to determine the presence and nature of a free radical in the compound.
8) Which of the following is true about the base peak in mass spectrometry?
A) The m/z value equals the molecular weight of the compound.
B) The m/z value corresponds to a very stable carbanion.
C) It has the largest peak height in the spectrum.
D) It has the highest m/z value of all the peaks in the spectrum.
E) The base peak is assigned a relative abundance equal to that of the parent ion.
9) What m/z value would you predict for the most stable fragment peak in the mass spectrum of
4-ethylheptane?
A) 128
B) 127
C) 113
D) 99
E) 85
10) How could you distinguish the mass spectrum of 2, 2-dimethylpropane from that of
isopentane?
Answer: The loss of a methyl from 2, 2-dimethylpropane forms a stable tertiary carbocation,
while loss of a methyl from isopentane forms a less stable secondary carbocation. So the M-15
peak will be greater for 2, 2-dimethylpropane.
Section: 13-2
11) 2-Methylhexane shows an intense peak in the mass spectrum at m/z = 43. Propose a likely
structure for this fragment.
Answer: (CH3)2CH+
Section: 13-2
12) Which of the following is not a major peak in the MS of isopentane?
A) 29
B) 43
C) 57
D) 60
E) 72
Answer: D
Section: 13-2
13) Which of the following is not true about the M+1 peak?
A) It is one m/z unit higher than the base peak.
B) It is one m/z unit higher than the molecular ion peak.
C) It is one m/z unit higher than the parent ion peak.
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D) It occurs because there is more than one naturally occurring isotope of carbon.
E) This means that the number of carbon atoms in a compound can be calculated if the relative
abundance of both the M and M+1 peaks is known.
14) Which of the following statements best explains how a hydrocarbon can show an M+2 peak
in mass spectrometry?
A) from 13C and 1H
B) from 12C and 2H
C) from a single 13C
D) from a single 3H
E) from two 13C's
15) Predict the molecular formula of the compound represented below based on the MS data
given.
m/z
84
85
86

Intensity
10.00
0.56
0.04

A) C6H12
B) C5H24
C) C4H6O2
D) C3H8O2
E) C5H8O
Answer: E
Section: 13-3
16) Which of the following characterizes the unusually intense peak of alkyl chlorides in MS
spectrometry?
A) M + 1 peak
B) M + 2 peak
C) base peak
D) parent peak
E) none of the above
17) Which compound's mass spectrum shows peaks at M, M+2, and M+4 whose abundances are
in a ratio of 1:2:1?
A) cyclohexanol
B) chlorocyclohexane
C) 1,2-dichlorocyclohexane
D) 1-bromopentane
E) 1,5-dibromopentane

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18) Is it possible to have an M + 2 peak in mass spectrometry? Explain.


Answer: A mass spectrum can show an M + 2 peak for a compound with a relatively abundant
isotope two mass units greater than the most common isotope (such as oxygen, chlorine, and
bromine) or for a compound that contains two isotopes that are one mass unit heavier than the
most abundant. The presence of a relatively large M + 2 peak is evidence for a compound with
chlorine or bromine. For instance, if M + 2 is 1/3 the height of the molecular ion, the compound
contains chlorine. If M + 2 is about the same height as that of the molecular ion, the compound
contains bromine.
Section: 13-3
20) Describe the molecular ion region in the mass spectrum of CH3CH2Br.
Answer: The natural abundance of the isotopes 79Br and 81Br are about the same; therefore,
there will be peaks of equal intensity at m/z 108 and 110.
Section: 13-3
21) A compound shows a molecular ion peak at m/z 167. The relative intensities of the M and
M+1 peaks are 50.0 and 4.4 respectively. How many carbons are in each molecule of the
compound?
Answer: 8
Section: 13-3
23) Which of the following m/z values is the base peak for benzyl alcohol?

A) 77
B) 108
C) 91
D) 17
E) 52
24) Which of the following compounds exhibits the pattern of m/z values shown below?
41, 43, 57, 87, 101, 116
A) propylbromide
B) isopropyl bromide
C) sec-butyl isopropyl ether
D) 2-hexanol
E) 2-butanone

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25) Which of the following is the base peak for the compound below?

A) 77
B) 92
C) 15
D) 57
E) 43
26) Which of the following structures will give a base peak of 43 in mass spectrometry?
A)

B) CH3CH2CH2CH2CH2CH3
C)

D)

E) none of the above


27) The mass spectra of alcohols often fail to exhibit detectable M peaks but instead show
relatively large ________ peaks.
A) M+1
B) M+2
C) M-16
D) M-17
E) M-18

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28) Which of the following m/z values is least intense in the mass spectrum of 1-chloropropane?
A) 80
B) 79
C) 78
D) 65
E) 63
Answer: B
Section: 13-5
29) Which of the following is/are true about the MS of 1-bromobutane?
A) Peaks of approximately equal intensity are observed at m/z 136 and 138.
B) The major fragmentation occurs by cleavage of the C-Br bond.
C) The most intense peak occurs at m/z 43.
D) both A and B
E) both B and C
Answer: D
Section: 13-5
30) An acylium ion is often produced as a fragment in the MS of which of the following class of
organic compounds?
A) ketones
B) ethers
C) alkyl halides
D) alcohols
E) peroxides
Answer: A
Section: 13-5
31) Show the m/z values of the molecular ion and 5 likely fragments for the compound ethyl
ether, CH3CH2OCH2CH3
Answer: 74, 59, 45, 44, 30, 29, 15
Section: 13-5
32) Provide the structure of the two ions which result when the molecular ion of 2methoxypentane undergoes fragmentation by -cleavage.
Answer:
+
+
CH3CH2CH2CHOCH3 CH3CHOCH3

Section: 13-5

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33) Provide the structure of the species which results when the molecular ion of 4-heptanone
undergoes fragmentation via a McLafferty rearrangement.
Answer:

Section: 13-5
34) Which of the following statements is not true about electromagnetic radiation?
A) The velocity of light is directly proportional to the energy.
B) All molecules absorb electromagnetic radiation at some frequency.
C) Frequency is inversely proportional to wavelength.
D) Energy is directly proportional to frequency.
E) Energy is inversely proportional to wavelength.
Answer: A
Section: 13-7
35) Which of the following regions of the electromagnetic spectrum has the greatest energy per
photon?
A) visible
B) microwave
C) radio
D) ultraviolet
E) infrared
Answer: D
Section: 13-7
36) Which of the following normally occurs in a molecule when a photon of infrared light is
absorbed?
A) An electron moves to an orbital of higher potential energy.
B) The vibration energy increases.
C) An electron changes alignment in a magnetic field.
D) The molecule gains an electron.
E) The molecule loses an electron.
Answer: B
Section: 13-7
37) How many centimeters (cm) are there in one micrometer (m)?
A) 10-6
B) 10-3
C) 10-5
D) 10-8
E) 10-4
Answer: E
Section: 13-7

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38) Which of the following is highest in energy per photon?


A) electromagnetic radiation with a wavenumber of 10-2 cm-1
B) electromagnetic radiation with a frequency of 107 cm/s
C) electromagnetic radiation with a frequency of 105 cm/s
D) electromagnetic radiation with a wavelength of 10 cm
E) electromagnetic radiation with a wavenumber of 106 cm-1
Answer: D
Section: 13-7
39) In the electromagnetic spectrum, ________ frequencies, ________ wavenumbers, and
________ wavelengths are associated with high energy.
A) high, small, long
B) low, large, short
C) low, small, short
D) high, large, short
E) high, small, short
Answer: D
Section: 13-7
40) An infrared wavelength of 4.48m is equivalent to a wavenumber of ________ cm-1.
Answer: 2230
Section: 13-7
41) Which has the higher speed in a vacuum, ultraviolet or infrared light?
Answer: They have the same speed.
Section: 13-7
42) Which region of the electromagnetic spectrum, IR or UV, contains photons of the higher
energy?
Answer: UV
Section: 13-7
43) Which region of the electromagnetic spectrum, radio or visible, is characterized by waves of
shorter wavelength?
Answer: visible
Section: 13-7
44) Which region of the electromagnetic spectrum, IR or X-ray, is characterized by waves of
lower frequency?
Answer: IR
Section: 13-7
45) Arrange the following regions of the electromagnetic spectrum in order of decreasing
wavelength: microwaves, visible light, ultraviolet light, infrared radiation, X-rays.
Answer: microwaves > infrared radiation > visible light > ultraviolet light > X-rays
Section: 13-7

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46) Which of the following are considered to be bending (in-plane) vibrations?


A) scissoring and wagging
B) scissoring and twisting
C) rocking and wagging
D) rocking and twisting
E) scissoring and rocking
Answer: E
Section: 13-8
47) Which of the following solvents is best used in infrared spectroscopy?

A) I
B) II
C) III
D) IV
E) V
Answer: B
Section: 13-8
48) Which of the infrared regions is considered to be the fingerprint region?
A) 4000cm-1 - 1000cm-1
B) 4000m - 1000m
C) 2200m - 1000m
D) 1000cm-1 - 400cm-1
E) 1000m - 400m
Answer: D
Section: 13-8
49) Which of the following is not a common bending vibration of a CH2 group?
A) flip
B) rock
C) scissor
D) twist
E) wag
Answer: A
Section: 13-8

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50) Which of the following increases the absorbance of a solution of phenol in ethanol?
A) increasing the amount of phenol in the solution
B) decreasing the amount of ethanol in the solution
C) decreasing the light path through the solution
D) both A and B
E) both B and C
Answer: D
Section: 13-8
51) While cleaning the organic stockroom, a student found a bottle of ethanol labeled "Denatured
with Benzene." He decided to determine the concentration of benzene in the ethanol by acquiring
the UV spectrum of the liquid in a 2.0 cm cell. The spectrum exhibited an absorption band at 260
nm which was attributable to benzene, and the absorbance of this band was 0.69. In a reference
source, the student found that the molar absorptivity of this benzene band in ethanol was 230 M1cm-1. Show how the student calculated the concentration of the benzene in the ethanol.
Answer:
A = cl c = A/l
c = (0.69)/(230 M-1cm-1)(2.0 cm)
c = 0.0015 M
Section: 13-8
52) Which molecule below has a significant band in the IR at 3400 cm-1 (strong and broad)?
A) CH3CH2CH2OH
B) CH3CCCH2CH3
C) CH3CH2CH(NH2)CH3
D) (CH3)3N
E) CH3CO2CH2CH3
Answer: A
Section: 13-9
53) Which molecule below has a significant band in the IR at 2220 cm-1 (medium)?
A) CH3CH2CH2OH
B) CH3CCCH2CH3
C) CH3CH2CH(NH2)CH3
D) (CH3)3N
E) CH3CO2CH2CH3
Answer: B
Section: 13-9

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54) Which molecule below has a significant band in the 1720 - 1780 cm-1 range of its IR
spectrum?
A) CH3CH2CH2OH
B) CH3CCCH2CH3
C) CH3CH2CH(NH2)CH3
D) (CH3)3N
E) CH3CO2CH2CH3
Answer: E
Section: 13-9
55) Which of the following statements best explains the information we can gain from infrared
spectroscopy?
A) It allows us to determine the number of protons in a compound.
B) It allows us to determine the kinds of functional groups in a compound.
C) It allows us to determine the molecular weight and the mass of some fragments of a
compound.
D) It allows us to determine the presence and nature of a carbocation in the compound.
E) It allows us to determine the presence and nature of a free radical in the compound.
Answer: B
Section: 13-9
56) Which compound would be expected to show intense IR absorption at 1715 cm-1?
A) CH3CH2CO2H
B) 1-hexene
C) 2-methylhexane
D) CH3CH2CH2NH2
Answer: A
Section: 13-9
57) Which compound would be expected to show intense IR absorption at 1746 cm-1?
A) CH3CH2OCH2CH3
B) CH3CO2CH3
C) CH3CH2CCH
D) CH3CH2SCH3
Answer: B
Section: 13-9
58) Which of the following wavenumbers corresponds to the bond shown below?
CC
A) 1650 cm-1
B) 2100 cm-1
C) 1100 cm-1
D) 3300 cm-1
E) 2850 cm-1
Answer: B
Section: 13-11
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59) Which of the following carbonyl groups exhibits the highest wavenumber in infrared
spectroscopy?

A) I
B) II
C) III
D) IV
E) V
Answer: C
Section: 13-12
60) Which compound would be expected to show intense IR absorption at 2710 and 1705 cm-1?
A) CH3COCH2CH3
B) PhCOCH3
C) PhCHO
D) CH2CHCOCH3
Answer: C
Section: 13-16
61) Which compound would be expected to show intense IR absorption at 2250 cm-1?
A) CH3CH2CH2CO2H
B) CH3CH2CH2CN
C) CH3CH2CH2CH2OH
D) CH3CH2CH2CONH2
Answer: B
Section: 13-16
62) Which of the following functional groups typically exhibits a carbonyl stretch at the lowest
frequency?
A) amide
B) ester
C) ketone
D) aldehyde
E) ether
Answer: A
Section: 13-12
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63) Which of the following species has a characteristic absorption at 2200 cm-1 in its IR
spectrum?
A) PhCH2CN
B) PhCH2N(CH3)2
C) PhCH2CO2CH3
D) PhCH2CH2OH
E) PhCH2OCH3
Answer: A
Section: 13-16
64) Which of the following species has a characteristic broad absorption at 3200-3500 cm-1 in its
IR spectrum?
A) PhCH2CN
B) PhCH2N(CH3)2
C) PhCH2CO2CH3
D) PhCH2CH2OH
E) PhCH2OCH3
Answer: D
Section: 13-16
65) Which of the following species has a characteristic absorption at 1250 cm-1 in its IR
spectrum?
A) PhCH2CN
B) PhCH2N(CH3)2
C) PhCH2CO2CH3
D) PhCH2CH2OH
E) PhCH2OCH3
Answer: C
Section: 13-16

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66) Which of the following carbon-hydrogen bonds exhibits the lowest wavenumber for a CH
stretch in infrared spectroscopy?

A) I
B) II
C) III
D) IV
E) V
Answer: B
Section: 13-16
67) Which compound would be expected to show intense IR absorption at 3300 cm-1?
A) CH3CCCH3
B) butane
C) 1-butene
D) CH3CH2CCH
Answer: D
Section: 13-16
68) Which of the following species has a characteristic absorption at 3300 cm-1 in its IR
spectrum?
A) (CH3)2CHCCH
B) (CH3)2CHN(CH3)2
C) (CH3)2CHCCCH3
D) (CH3)2CHCH=CH2
E) (CH3)2CHCO2CH3
Answer: A
Section: 13-16
69) Which molecule below has two significant bands (medium and broad) in the 3300 - 3500
cm-1 range of its IR spectrum?
A) (CH3)3N
B) CH3CH2NH2
C) CH3CH2NH2
D) CH3CON(CH3)2
E) CH3OCH2CH2N(CH3)2
Answer: C
Section: 13-16

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70) Which compound's carbonyl stretch occurs at the greatest wavenumber?


A) CH3CH2CH2CHO
B) CH3COCH2CH3
C) CH3CH2CONH2
D) CH3CH2CO2CH3
E) CH3CH2COCH2CH3
Answer: D
Section: 13-12
71) Which compound's carbonyl stretch occurs at the lowest wavenumber?
A) CH3CH2CH2CHO
B) CH3COCH2CH3
C) CH3CH2CONH2
D) CH3CH2CO2CH3
E) CH3CH2COCH2CH3
Answer: C
Section: 13-12
72) Which molecule below has a significant band in the IR at 3300 cm-1 (medium and sharp)?
A) 1-pentene
B) cyclohexane
C) 2-heptyne
D) 1-pentyne
E) diethyl ether
Answer: D
Section: 13-16
73) Which molecule below has two significant bands in the IR at 2720 cm-1 and 2820 cm-1
(medium)?
A) CH3COCH2CH
B) CH3CH2CO2CH3
C) CH2=CHCH2CH3
D) CH3CH2CH2CHO
E) CH3CH2CH2OH
Answer: D
Section: 13-16
74) Does the position of the stretch of the oxygen-hydrogen bond in alcohols depend on the
concentration of the alcohol?
Answer: Yes, the more concentrated the alcohol, the more likely it is for the alcohol to form
intermolecular hydrogen bonding. So the OH group of a concentrated (hydrogen-bonded)
solution absorbs at a lower wavenumber than that of the diluted solution.
Section: 13-12

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75) Which has a lower characteristic stretching frequency, the C-H or C-D bond? Explain briefly.
Answer: C-D; heavier atoms vibrate more slowly.
Section: 13-12
76) Which has a lower characteristic stretching frequency, the C=O bond or the C-O bond?
Explain briefly.
Answer: Stronger bonds are generally stiffer, thus requiring more force to stretch or compress
them. The C-O bond is the weaker of the two and hence has the lower stretching frequency.
Section: 13-12
77) Explain how hydrogen bonding affects the shape of O-H and N-H absorption bands in IR
spectra.
Answer: O-H and N-H bands are generally quite broad. These bands are broad because the
hydrogen bonds vary in strength. The more concentrated the sample, the more likely
intermolecular hydrogen bonding can occur.
Section: 13-12
78) Which of the following functional groups will exhibit no IR absorption at 1630 - 1780 cm-1
or at 3200 - 3550 cm-1?
A) an alcohol
B) an amide
C) a ketone
D) an aldehyde
E) an ether
Answer: E
Section: 13-14
79) How could IR spectroscopy be used to distinguish between the following pair of
compounds?
(CH3)3N and CH3NHCH2CH3
Answer: N-H absorption near 3300 cm-1
Section: 13-14

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80) In which of the following molecules is the presence of the IR peak for CC not observed?
A)

B)

C)

D)

E)

Answer: A
Section: 13-15
81) Ethyne (HCCH) does not show IR absorption in the region 2000-2500 cm-1 because:
A) C-H stretches occur at lower energies.
B) CC stretches occur at about 1640 cm-1.
C) there is no change in the dipole moment when the CC bond in ethyne stretches.
D) there is a change in the dipole moment when the CC bond in ethyne stretches.
Answer: C
Section: 13-15

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82) Which of the following compounds has a vibration that is infrared inactive?
A) CH3CCH
B) H2O
C)

D) CO2
E) CO
Answer: D
Section: 13-15
83) Which compound's CC IR band is weakest, 1-butyne, 2-pentyne, or 3-hexyne? Why?
Answer: The CC band of 3-hexyne is weakest. This vibration is IR inactive because no dipole
moment change occurs in the symmetric stretch.
Section: 13-15
84) Deduce a possible structure for the compound with the IR absorptions below.
C3H3Br: 3300, 2900, 2100 cm-1
Answer: HCCCH2Br
Section: 13-16
85) Deduce a possible structure for the compound with the IR absorptions below.
C3H5N: 3000, 2250 cm-1
Answer: CH3CH2CN
Section: 13-16
86) Deduce a possible structure for the compound with the IR absorptions below.
C5H8O: 3000, 1750 cm-1
Answer: cyclopentanone
Section: 13-16
87) Deduce a possible structure for the compound with the IR absorptions below.
C4H8O: 3000, 2800, 2715, 1715 cm-1
Answer: CH3CH2CH2CHO
Section: 13-16
88) How could IR spectroscopy be used to distinguish between the following pair of
compounds?
CH3OCH2CH3 and CH3CH2CH2OH
Answer: O-H stretch at 3300 cm-1
Section: 13-16
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89) How could IR spectroscopy be used to distinguish between the following pair of
compounds?
HOCH2CH2CHO and CH3CH2CO2H
Answer: Carboxylic acid will have a very broad O-H absorption; aldehyde has characteristic CH stretches.
Section: 13-16
90) In the UV-visible spectrum of (E)-1,3,5-hexatriene, the lowest energy absorption corresponds
to:
A) a to * transition.
B) a to * transition.
C) a to * transition.
D) a to * transition.
E) a to transition.
Answer: A
Section: 13-17
91) Absorption of UV-visible energy by a molecule results in:
A) vibrational transitions.
B) electronic transitions.
C) rotational transitions.
D) nuclear transitions.
E) none of the above
Answer: B
Section: 13-17
92) Which of the following methods is most suitable for studying conjugation in molecules?
A) infrared
B) NMR
C) mass spectrometry
D) X-ray
E) UV visible
Answer: E
Section: 13-17

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93) Which of the following compounds exhibits the highest max in UV spectra?

A) I
B) II
C) III
D) IV
E) V
Answer: D
Section: 13-19
94) Which of the following compounds absorbs the longest wavelength of UV-visible light?
A) (E)-2-butene
B) (Z)-2-butene
C) 1-hexene
D) (Z)-1,3-hexadiene
E) (E)-1,3,5-hexatriene
Answer: E
Section: 13-19
95) An increase in conjugation is correlated with ________ in the energy of the LUMO,
________ in the energy of the HOMO, and ________ in lmax.
A) a decrease, an increase, a decrease
B) a decrease, an increase, an increase
C) an increase, a decrease, a decrease
D) an increase, a decrease, an increase
E) an increase, an increase, a decrease
Answer: B
Section: 13-19
96) Is the max of phenol in aqueous solution affected by the pH of the solution? If so, explain
how and why max changes.
Answer: As the pH of the solution increases, an increasing amount of the phenol is converted
into the conjugate base, the phenolate ion. The max of the phenolate ion is greater than that of
phenol since an additional pair of nonbonding electrons is interacting with the aromatic ring.
This is known as a red shift.
Section: 13-19

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97) Which color is observed when a sample absorbs light at 650 nm?
A) yellow
B) orange
C) red
D) green
E) blue
Answer: E
Section: 13-20
98) When a solution of an organic compound absorbs light whose wavelength is 400 nm, the
solution appears ________.
A) yellow
B) red
C) purple
D) blue
E) white
Answer: A
Section: 13-20
99) When a solution of an organic compound absorbs light whose wavelength is 700 nm, the
solution appears ________.
A) yellow
B) green
C) red
D) orange
E) purple
Answer: B
Section: 13-20
100) The pKa of a compound whose acidic or basic form absorbs UV or visible light can be
determined spectroscopically since ________.
A) lmax always decreases as acidic form is converted to basic
B) the pKa is the same as the pH at which half of the total absorbance increase occurs
C) absorbance of the basic form is always twice that of the acidic form
D) absorbance of the acidic form is always twice that of the basic form
E) delocalization always leads to a decrease in acidity
Answer: B
Section: 13-21
101) How can UV spectroscopy be used to estimate the nucleotide composition of DNA?
Answer: The melting temperature of DNA is the midpoint of an absorbance-versus-temperature
curve. The melting temperature increases with the number of G-C base pairs so it can be used to
estimate composition.
Section: 13-21

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102) Give the ion that corresponds a m/z ratio of 31 in a mass spectrum of 1-butanol.
A)
B)
C)
D)
E)
Answer: B
Section: 13-5
103) Give the ion that corresponds to a m/z ratio of 56 in a mass spectrum of 1-butanol.
A)
B)
C)
D)

E) none of the above


Answer: C
Section: 13-5
104) Give the m/z ratio of the molecular ion in the mass spectrum of 1-butanol.
Answer: 74
Section: 13-2

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105) Give the ion that corresponds to a m/z ratio of 58 in a mass spectrum of 2-pentanone.
A)

B)
C)

D)
E)

Answer: A
Section: 13-5
106) Give the ion that corresponds to a m/z ratio of 43 in a mass spectrum of 2-pentanone.
A)
B)
C)
D)
E)
Answer: A, B
Section: 13-5
107) Give the m/z ratio that corresponds to the molecular ion in the mass spectrum of 2pentanone.
A) 28
B) 43
C) 58
D) 71
E) 86
Answer: E
Section: 13-2
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108) Give the m/z ratio that corresponds to the molecular ion in the mass spectrum of 2bromobutane.
Answer: 136 and 138
Section: 13-3
109) Give the fragment(s) that corresponds to a m/z charge of 58 for ethylpropylamine.
A)
B)
C)
D)
E)
Answer: A, B
Section: 13-5
110) Give the m/z ratio that corresponds to the molecular ion in the mass spectrum of
ethylpropylamine.
Answer: 87
Section: 13-2
111) Identify the bond with the lowest wavenumber in the IR spectrum.
A) C=O
B) C-O
C) O-H in alcohol
D) N-H
E) C-H
Answer: B
Section: 13-9
112) In the infrared spectrum, a compound of formula C4H8O gave an absorption band at 1720
cm-1, but no bands at 2720 - 2830 and 3400 cm-1. What is the compound?
A) 2-butanone
B) butanal
C) cis-2-butenol
D) trans-2-butenol
E) 1-butenol
Answer: A
Section: 13-16

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113) Describe the similarities and differences in the infrared spectra of methyl propanoate and
butanoic acid.
Answer: Both compounds give an infrared absorption band at 1700 cm-1. The acid has an
additional peak at 3000 cm-1.
Section: 13-16
114) Identify the compound that has a formula of C5H10 and bending vibrations at 990 and 910
cm-1.
A) 1-pentene
B) cis-2-pentene
C) trans-2-pentene
D) 2-methyl-1-butene
E) 2-methyl-2-butene
Answer: A
Section: 13-11
115) Identify the compound that has a formula of C4H9N and has one absorption band at 3400
cm-1 and a doublet at 1380 cm-1.
A) diethylamine
B) methylpropylamine
C) isopropylmethylamine
D) butylamine
E) dimethylethylamine
Answer: C
Section: 13-16
116) Identify the compound that has a formula of C3H6O with a stretching vibration at 1050 cm1 and an absorption band at 3400 cm-1, but no doublet at 1380 cm-1.
A) 1-propanol
B) 2-propanol
C) ethyl methyl ether
D) propen-1-ol
E) propen-2-ol
Answer: A
Section: 13-16
117) Give the C-H absorption band for a sp carbon.
A) 2700 cm-1
B) 2900 cm-1
C) 3100 cm-1
D) 3300 cm-1
E) 3500 cm-1
Answer: D
Section: 13-11

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118) A mixture of two compounds give absorption bands at 1470, 1595, 1700, 2720, and 2740
cm-1. What compounds are present?
A) aldehyde + benzene
B) ketone + benzene
C) ester + benzene
D) carboxylic acid + benzene
E) anhydrice + benzene
Answer: A
Section: 13-16

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